Uses
1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride is a perylene derivative used in the preparation of fluorofluorescent perylene bisimides for use in perfluorinated liquids. The fluorescence of 1,6,7,12-Tetrachloroperylene tetracarboxylic acid dianhydride has made it a viable target for use as fluorescent liquid crystals.
Synthesis
3,4,9,10-tetracarboxylic dianhydride (3.30 g, 8.41 mmol) was used as a raw material, mixed with chlorosulfonic acid (20 mL, 300 mmol) and iodine (0.56 g, 2.20 mmol), and the reaction was stirred for 30 hours at 65 °C. Upon completion of the reaction, the mixture was cooled to room temperature and subsequently added slowly dropwise to an ice-water mixture. The precipitated red solid product was collected by filtration in a yield of 4.14 g in 92% yield. The product was analyzed by 1H NMR (d-DMSO, ppm) showing: 8.75 (s, 4H, aryl proton). 13C NMR (d-DMSO, ppm) analysis showed: 119.75, 125.29, 129.5, 134.88, 136.22, 158.16, 168.53. mass spectral (EI) analysis showed: m/z 532.
References
[1] Journal of the American Chemical Society, 2008, vol. 130, # 26, p. 8271 - 8279
[2] Synlett, 2018, vol. 29, # 19, p. 2509 - 2514
[3] Journal of the American Chemical Society, 2015, vol. 137, # 15, p. 5210 - 5224
[4] ACS Combinatorial Science, 2016, vol. 18, # 12, p. 723 - 739
[5] Polymer, 2014, vol. 55, # 23, p. 6058 - 6068
